Acetic Acid → Tert-butyl 3-(diethylamino)benzylcarbamate

HRID 2071003노트

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HRID 2071003 반응식
[CH:1](=O)[CH3:2].[NH2:4][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[BH3-]C#N.[Na+].[CH3:24][C:25](O)=O>CC#N.O>[CH2:24]([N:4]([CH2:1][CH3:2])[C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:25]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

생성물 1

HCID 68671365Tert-butyl 3-(diethylamino)benzylcarbamate수율 77%

시약·촉매·용매 1

HCID 18373917Acetonitrile--water (1/1)용매

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온도
0 °C

실험 절차

Acetaldehyde (0.52 ml, 0.4 g, 9.08 mmol, 5 eq) was added to a stirred solution of tert-butyl 3-aminobenzylcarbamate (derived from 3-(aminomethyl)aniline (TCI America)) in 11 ml CH3CN/H2O (10:1) at 0° C. After 5 min NaBH3CN (0.3 g, 4.54 mmol, 2.5 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc and stirred at 0° C. for 5 min. The ice-bath was removed and the reaction was stirred at room temperature for 45 min. The solvent was removed in vacuo. The residue was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.3875 g (1.4 mmol, 77% yield) of tert-butyl 3-(diethylamino)benzylcarbamate.

후처리

  1. customThe ice-bath was removed
  2. stirringthe reaction was stirred at room temperature for 45 min
  3. customThe solvent was removed in vacuo
  4. additionThe residue was diluted with saturated aqueous NaHCO3
  5. extractionextracted with EtOAc (×2)
  6. washThe combined organics were washed with water (×3), brine (×1)
  7. dry with materialdried over Na2SO4
  8. filtrationThe inorganics were filtered off
  9. customthe solvent was removed in vacuo
  10. customPurification via flash chromatography

출처 및 근거

ORD 기록
ord-6923e1b0b96f4fe4a12f762793e92e89
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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